You’ve written lots of blog posts, and maybe you’ve even organized them using categories and tags. But your readers are still getting lost. They like the posts they’ve found using search engines, but they don’t know where to go next. If they click on your categories or tags, they see your newest posts, but they might not find your most useful ones or figure out a good order to read posts in. Sure, if you wrote all your posts according to a well-planned editorial calendar, people can follow that sequence. (If only we could all be so organized!)

I know what that’s like. I’ve got thousands of posts in my archive, and even I find it hard to navigate through them. I’ve tried all sorts of plugins for suggesting related posts, but I didn’t find any that could suggest good relevant content quickly.

How can we help people find the posts they need? Adding a “Popular Posts” widget to the sidebar is one way to help people discover your posts, but it only shows a handful of entries. A better way to help lost readers is to put together a page with links to your recommended posts. You can call it Resources, Start Here, or a similar title, and add a prominent link to your menu or sidebar. Off the top of your mind, you can probably think of a few blog posts to include on a resources page. Add those to the page and start helping your readers.

When you have a little more time, gradually incorporate more links into that page. You’ll still want to highlight the key posts people should begin with, but after that (short) list, you can add more lists of recommended posts by topic. Choose your most important category and review the posts within it. Copy the titles and links from your blog posts and arrange them in a logical order, using either a list or an outline. For example, you might go from a list like:

Post 1

Post 2

Post 3

Post 4

Post 5

to an outline like:

Subtopic 1

Post 1

Post 3

Subtopic 2

Post 2

Post 4

Post 5

As you get an overview of your posting history, you might find opportunities to summarize several posts into a longer guide, update and improve previous posts, and fill in the gaps with additional posts. Add these ideas to your editorial calendar or idea notebook, and use those ideas the next time you sit down to write.

What do I mean when I say that I want to get better at outlining? What can outlining help me with, anyway?

Outlines are good for:

Capturing thoughts quickly: You don’t have to write full sentences. You can add keywords or phrases in any order, and you can flesh them out later.

Writing non-linearly: You don’t have to write one paragraph after another. You can jot down your key point, come up with a few supporting points, and then think about your introduction or conclusion.

Organizing your thoughts: You don’t need to always go from topic to detail. You can capture random thoughts and then group them afterwards.

Deciding on depth and coverage: How much detail should you include? What subtopics do you want to cover, and what will you save for another post? What can you cut, and what’s missing? An outline can help you discover these things before you spend a lot of time writing.

Rearranging topics for a more logical flow: Does it make sense to discuss one idea before the other? Fixing the flow in your outline saves you from rewriting all the transitions.

Writing quickly: If you’ve mapped out what you want to talk about, you don’t have to worry as much about writer’s block – all you have to do is follow the trail.

Picking things up where you left off: If you’re writing something that you can’t finish in one sitting (or if you want to be able to revise it easily even after some time), an outline helps you remember what you want to say and see what you need to do next.

Let me break outlining into sub-skills and think about different ways I can practise each of them.

Outlining a single blog post

Reverse outlining

Outlining link-heavy posts or summary posts

Outlining larger resources and books

Outlining lifelong learning

1. Outlining a single blog post

I tend to write short blog posts focusing on a single question I want to explore or a point I want to make. This results in posts that are usually somewhere between 400 and 2,000 words. Although I’m comfortable with this way of working, I think outlining can help me organize my posts more effectively. Writing in paragraphs sometimes gets in the way of seeing the post as a whole or tweaking its flow easily. If I make an outline and then transform it into text, I find it easier to keep the whole post in mind as I write.

Because I use Org Mode for Emacs to write, it’s easy for me to work with outlines. I can hide and show parts of my outline using keyboard shortcuts. I can also keep a copy of the outline in one part of my window while I rewrite another copy of the outline into the actual text.

In addition to practising by outlining posts like this one, I can double-check the flow of a post while it’s in outline form, and I can also try different permutations of the order.

2. Reverse outlining

To create a reverse outline, start with an existing text. Identify the key points of each paragraph, and create an outline based on that. Organize those points into a more complex structure as needed.

I sometimes use reverse outlines with my own posts or drafts if I get the sense that things are a little out of order, but I can’t pin down why. With Org Mode, I can add list items before each paragraph, summarizing their key points. Then I can manipulate those list items with keyboard shortcuts, hiding the paragraphs or moving them around. When I’m happy, I can remove the outline structure and go back to working with paragraphs.

Reverse outlines are also useful when studying other people’s writing for content or for structure. They help you see the text as a whole instead of getting lost in paragraphs. I don’t do as much of this as I could. If I spent more time reverse-outlining posts that appealed to me, I could probably learn more about techniques for writing.

In addition to practising by creating reverse outlines for my posts and other people’s writing, I might find it useful to tweak Emacs for reverse outlining. I could write a function that automatically structures paragraphs into list items, and another function that extracts the paragraphs from the outline. Hmm…

3. Outlining link-heavy posts or summary posts

This is one step up from posts that deal with a single thought.

It can be challenging to write a blog post that links to lots of other blog posts. I find myself wondering where I want to go into more detail, how to avoid restating so much, how to bridge the different topics, and how to reconcile various types of writing.

I find outlines helpful for thinking about the structure of the post.

Should I bring in background information and then focus on a single question, exploring that in the body of the post?

Are the links tangential to the post, pointers for further exploration?

Am I trying to explain something to someone, and can I use links to let them dive down to the level of detail they want?

Outlines help me keep track of possible ideas to add and how to connect the different topics.

I write many posts that use links for background information or tangents, and the process for these is similar to the one for outlining a single blog post.

I don’t write many summary posts, though, and that’s something that I could practice. To do this well, I could pick more things that people want to learn (such as Emacs and Org) and write high-level overviews that link to more details.

One of the things getting in my way when it comes to working on summary posts, I think, is that it’s easy to pick the immediate benefit of moving myself forward a little, over the long-term benefit of teaching others (whom I could eventually learn from too). I can remind myself that I have plenty of time to write those exploratory posts, and that writing summary posts helps me consolidate, test, and share what I know.

4. Outlining larger resources and books

This is quite a few steps up from writing summary posts. I am not at all good at this yet, and will probably take a few years (at least!) to get the hang of it.

I tend to focus on writing the parts that are most interesting for me, so outlines sometimes make me feel guilty about the gaps. It turns out that working with existing material or committing to small chunks helps me get around challenges with motivation. I also do much better developing things in the open, getting feedback from people and revising things on the fly.

I’m looking forward to practising with 12-week courses, which make sense as the next small step to take.

5. Outlines for lifelong learning

Outlines can help with more than books and blog posts. I think they can help me learn overall, too. I think they might give me a way to place what I’m learning in context, connect things with other things I’ve learned or that I’m working on learning, capture threads that I’m not planning to investigate at the moment, and let me follow up with those threads when I want to revisit them.

I periodically update my learning plans, but I could give this more attention. Most of my learning notes are in my other Org files: rough notes by date in my journal, blog posts by topic in my index, outlines for things to write about in my sharing outline, and a high-level overview of evil plans.

There’s probably a better way to do this – perhaps incorporating my learning outline into my weekly and monthly review? I haven’t quite figured out how to combine past, present, and future in outlines in a way that makes sense to me while still making it useful to other people, like the way my blog index is useful because it’s not cluttered with other irrelevant points. Hmm.

Next steps

I hadn’t realized it before writing this post, but writing summaries and tiny guides (post-length, not book-length) would be a good in-between step for learning more about outlining before trying to tackle larger projects like books. A 12-week course of short tips might be interesting to do, too.

I’ve been working on a habit of drawing daily. It turns out to be a useful tool for exploring thoughts. I start with a question or an idea, and draw or write in the process of thinking about it. Since my blog posts usually deal with one thought at a time too, the drawings become good starting points for blog posts: I draw, and then I flesh it out with words. (Like this post!)

Before I started drawing my thoughts, I worked with a huge text-based outline of things I wanted to write. The outline was really handy for sketching out an idea or jotting down my thoughts before I got distracted by research or other things. It was also great for tweaking the logical flow of a blog post or how it fit into a possible blog post series before I actually sat down to write paragraphs.

Both drawings and text outlines have their advantages. How can I better integrate drawing into the process of writing or blogging?

When: Drawing works well for me as a low-energy activity late at night, when I’ve already put my computer away or I don’t want to be tempted into staying up late staring at a screen. My hands get tired if I draw for a long time, though. Writing works well for me during the day, because I can write faster and I can reorganize things quickly. That suggests that I should draw as a way of preparing my thoughts in the evening, sleep on it, and then flesh ideas out by writing during the day.

Level of detail: Text-based outlines are good for my overall outline because I can work with lots of unrelated topics. Drawing is good for high-level maps of a single topic (like this one for learning) because I can keep the drawing in front of me as I explore. Drawing is also good at the level of a single thought or question, but I can’t draw to the same level of detail that I can capture in a text outline. If I’m planning a large topic, then, I might:

use text for the overall outline,

draw a map of topics to explore,

copy the map into my outline and drill down until I get to the level of individual questions or ideas,

draw the idea as a way to explore it,

then outline further details, especially if I’m planning a series of posts

I’m also curious about using more flexible mindmappers like Freeplane to do some of my mapping on the computer. I prefer Org Mode text outlines over straightforward mindmaps like Freemind because they have essentially the same structure but I’m more comfortable with text manipulation in Org, but Freeplane’s floating nodes might be interesting to play with.

I wonder who else out there uses sketchnotes, mindmaps, or drawings as part of their writing process. Do you use them, or have you come across other writers who do? I’d love to hear from you in the comments!

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JohnKitchin Thanks. That matches my current understanding too. It seems like use-package pretty conveniently installs and configures packages. I have seen cask for creating and installing... – Emacs configuration and use-package